Momentum building: Trucker of the Month Sam Kelly, 3 trucks and counting

With this week’s edition of the Overdrive Radio podcast, hear my talk with Black Sheep Express three-truck owner-operator and "problem-solver" Sam Kelly, headquartered in Mississippi and Overdrive's April Trucker of the Month, putting him in the running as a semi-finalist for our Trucker of the Year award for 2026.

If you or your small fleet, up to three trucks, exceled through the rough years since the big fuel run-up and rates shock of 2022, if you’ve persevered through all of that turmoil,  you’re no doubt a worthy contender. Get your business in the running at this link. 

Here’s wishing everyone in the audience a Memorial Day honoring the fallen for the freedoms we enjoy here in the United States. For this week’s podcast, a different sort of honor for Kelly, leased now to CST Lines of Wisconsin in a refrigerated freight operation.

[Related: The problem-solver: Trucker of the Month Sam Kelly's big biz comeback]

Kelly and his two drivers, Bubba Rushing and Rodriguez Byrd, pull a dedicated load outbound from Wisconsin to California, and in the self-dispatch program at CST Kelly otherwise negotiates and books brokered freight on his own. 

Often, they're completing a triangle on the return with the Southeast and/or Washington State as the midpoint, depending on the season.

Business

Overdrive's Load Profit Analyzer

Know your costs, owner-operators? Compute the potential profit in any truckload, access per-day and per-mile breakouts, and compare brokers' offers on multiple loads. Enter your trucking business's fixed and variable costs, and load information, to get started. Need help? Access this video to walk through examples with Overdrive’s own Gary Buchs, whose work assessing numbers in his own business for decades inspired the Analyzer to begin with.

Try it out!

Howes sponsors Overdrive Radio. The longtime trusted provider of fuel treatments like its Howes Diesel Defender all-weather mileage booster and winter Diesel Treat anti-gel / Lifeline rescue treatments to get you through the coldest temps. Find more information about all of Howes' products at the company website. Kelly separates himself from the crowd in myriad ways, and perhaps not least in his willingness to be that problem-solver, to take matters into his own hands when plans break down. But Kelly’s story is remarkable, too, with respect to a clear instinct to learn from his own errors in business and in life, adjust accordingly, and come out the other side no less eager to win even during hard times.

His drive toward business ownership in his early days trucking was such that he took a 40-some-cents-a-mile company driver job and basically lived in the truck to turn it all into a nest egg for a cash payment for his first power unit. It was a bit of a disaster, that truck, by his account, yet he persisted. 

When it came time to buy a house, too, he kept his long-term growth goals in focus. 

Lenders might look at your tax returns and "tell you, 'Hey you can buy this much house,'" he said. "No, you can't. Because there will be a thing that's going to be called hard times. For the house they approved me up to, I bought a third of it." 

Frugality, in essence, would be his wachword. When the rates crash hit starting in 2022 and things got tough thereafter, he nonetheless "never missed a mortgage payment." 

He had to make business adjustments in a big way, though. 

As in personal finance, as in business, too, for the owner-operator, who’s learned plenty lessons from those hard times, as you'll hear in this week's podcast:

Get your own business -- or nominate another owner to compete -- in the Trucker of the Year competition for 2026 via this link.

As mentioned, Overdrive Load Profit Analyzer: https://overdriveonline.com/load-analyzer